


Not so Ninja

by dustbunnies27



Category: Supernatural
Genre: 69 (Sex Position), Because prompts are fun, Bottom Dean, Cas is BAMF, Charlie Ships It, Dean is such a dork, M/M, Meet-Ugly, Morning Sex, Multi, Nerd Dean, Nipple Play, Punk Castiel, Rimming, Slight feminization, Smut will happen in later chapters, Top Castiel, but for now just a lot of swearing, stretching my writing muscles, will change rating to Explicit
Language: English
Status: In-Progress
Published: 2016-01-18
Updated: 2016-01-25
Packaged: 2018-05-14 19:06:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 7,988
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5754766
Author URL: https://archiveofourown.org/users/dustbunnies27/pseuds/dustbunnies27
Summary: <blockquote class="userstuff">
              <p>Based off a Meet-Ugly prompt I could not ignore because it sounds like the shit these two would get into:</p><p>"You're the bastard who keeps parking right in front of my house so I retaliated by keying your car and you caught me"</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Yay for Meet-Ugly AUs, because I'm bitter and Meet-Cutes are overrated! Enjoy and don't forget to comment!

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~  
“Yeah, so I was at the club right? And out of nowhere there was like this angel in the middle of the dance floor, she had long blonde hair and-”

Dean suddenly heard a thumping beat coming from outside his window, and the screech of tires.

“Charlie!”  
“What, I was in the middle of my story dude… anyways I -” Charlie huffed.  
“He’s back, Charlie. I can hear that fucking car outside my window again” Dean grumbled.  
“Wait who? Oh yeah, that douchebag that parks right in front of your driveway, right? Why don’t you go talk to him Dean?”

Dean peered out his window. Yup, that’s his car alright, fugly ass Honda Civic with that ridiculous sound system that is just straight up _obnoxious._

“I can’t just go talk to him Charlie, what if he’s some psychopath, and he pulls a fuckin’ knife on me or something? Or if he’s some drug lord that would kill me and my entire family if I even looked him in the eye?”  
“Oh my God, Dean stop being such a bitch! Every night you complain about that dude parking infront of your car, but you never do anything! Do you want me to come over there and kick his ass for you?” Charlie sneered. She really did love Dean, but his bitching was seriously cutting into her hot lady story time.  
“No no, I’m fine. Actually no, I’m not fine, I’m sick of this shit every damn night! I’m going to do something TONIGHT!” Dean yelled into the phone.  
“That’s more like it, bitch! Are you going to go confront him? Rough him up a bit, give him a taste of that Winchester right hook? You could totally give him a black eye, I would support you 100%!” Charlie tittered excitedly.

“Uh, no I was thinking of something more...reveng-y? Like maybe leaving a fake parking ticket on his car? Or like slashing his tires, ya know, Carrie Underwood style? Or actually I know, I’ll key the bastard’s car! Yeah he won’t know what hit him, and he’ll think that its not safe to park his precious car outside and he’ll park it in his fucking garage like a normal person!” Dean was determined.

This was Dean’s master plan: first wear all black, because well sneaking around calls for all black, and damn if he didn’t look good in all black. Next, sneak outside to Mr. Douchebag’s car and key the word DICK into the side of his door. Then run back into his house like the hounds of hell were on his heels themselves.  
“Seriously Dean, you’re gonna write DICK on his car? Have you suddenly turned into a pre-pubescent teenage boy?”  
“Shut up Red, that douchenozzle can’t know it’s me keying his car so I gotta make it believable! Okay I’m ready, I’m gonna go do it now, stay on the phone with me though...for moral support and stuff, like not because I’m scared or anything…” Dean mumbled, grabbing his keys and heading down the stairs.

Making it out the front door, Dean sidled up beside the driver’s door of Mr. Douchebag’s car. Bending down, he pulled out his key and made a small mark where he would start his _masterpiece._  
“Oh my God Charlie. Charlie. I’m going to do it, after months and months of this asshole parking right in front of my driveway he is going to get his just desserts. I’m going in for the kill..” Dean laughed, a tad bit maniacally.  
“ Ok Dean, I’m happy for you, a bit creeped out at how much joy you get from this but that’s okay I guess. I still think you should just talk to this dude. Like what if it’s some misunderstanding, and he’s super cool about it? What if you guys become friends because of this… wait Dean, what if he’s _super hot?_ You haven’t dated anyone since Michael, and that was months ago. Maybe you should wait…” Charlie was cut off by the screeching sound of metal on metal.  
“And you’ve already started haven’t you? You’re such a loser, Winchester.”  
“Yup,” Dean said, popping the p, “ already on the K… just gotta dot the i aaaand...I’m done! Fuck yeah! Dean Winchester -1, Mr. Douchebag - 0!” Dean declared, pumping his fist in the air and standing back up.  
“I feel so accomplished Red, I’m a fucking ninja of awesomeness, and I didn’t even get-” Dean turned around to walk home, and ran straight into a...wall? No, not a wall, a person, a very strong muscular body; okay so definitely a male then. _Fuck._

“Hello? Dean, are you there? Did you drop your fucking phone on the floor like the clumsy shit you are? Hello, Winchester I swear to God if you muted me…”

Dean took the phone down from his ear as he slowly looked up into, the bluest eyes he had ever seen. Scratch that, the angriest, bluest eyes he had ever seen.  
Still unable to speak, Dean watched the man, reach out and pluck his phone from his hand, lifting it to his ear.

“I think your friend is going to have to call you back, he has a _very_ pissed off neighbor to attend to.” The man said coolly into the phone, disconnecting the call to the cries and attesting of Charlie.

 _Well, so much for being a fucking ninja of awesomeness_ , Dean though.


	2. Chapter 2

**Notes for the Chapter:**

> So, I already have over 100 hits?!?!?!?!? This is awesome, okay you guys are the best!  
> This is the last chapter that will have no smut, so after this the rating is going up!  
> Yay for porn with a leetle bit of plot!  
> Also, who else feels like Punk!Castiel gives them life??

 

Dean shoved his keys in his pocket, putting distance between him and Mr. Scary-douchebag.

“Wow man, some luck huh? I saw some kids keying your car and I came down to scare them off and survey the damage, I, um guess I was too late huh?” Dean stammered, literally pulling his excuse out of his ass.

 

“Well, if by  _ kids _ you mean you in a black hat and scarf vandalizing my property,  _ very conspicuously _ , i might add, then yeah some luck.” The man deadpanned, passing Dean his cell phone and crossing his arms over his chest.

_ Fuck, so he did see me, what do I do? Oh god, this is the day I die, at least I won’t have to pay rent anymore… _ Dean was snapped out of his thoughts by the man clearing his throat.

 

“Um, okay so I guess you saw me, um the thing is, I uh, I didn’t know it was  _ your _ car per say, I just thought it was some random person’s car and I was having a bad day. Oh man I’m sorry I wasn’t thinking that was so fucking dumb of me, I-” Dean was rambling, this guy was going to kick his ass either way, yet he was just prolonging the inevitable.

 

“What’s your name?” The guy almost barked.

“Huh?” 

“Your name? I assume you have one, and it is getting really annoying calling you “guy who just keyed my car” in my head.” 

“Oh, yeah, um Winchester? Dean, Winchester.” Dean winced, why the ever-loving fuck did he just pull a James Bond? God, he was lame.

 

“Okay, Dean, so how are we going to work this out? I really don’t want to kick your ass right now,” Dean internally jumped for joy at that one, “but you damaged my car… So you need to pay me back somehow.” The man kept eye contact with Dean the whole time, it was a little intimidating to be honest, even though Dean was a bit taller than him.

 

Pulling off his beanie, Dean raked his hand through his dirty blonde hair. “ Shit, yeah man I’ll pay you back, its just… Could it like be in installments? My shifts at the store are being cut these past few weeks plus rent is in a week,” Dean flushed, shoving his hands in his hoodie pocket, “...Ok, so from what I know I can probably pay you like $50 right now, how much do you think it will cost to fix it up, I’ll google -”

“I don’t want you to literally pay me back Dean. I was thinking more of an  _ agreement _ between the two of us would work for me, don’t you?” Mr. Douchebag sneered, giving Dean a  _ very _ unnerving once over, eyes lingering on his lips for way too long. 

 

_ Oh,  _ Dean though,  _ he wants me to sleep with him? Well at least I won’t have to pay him with money, but he’s a stranger, and scary, and I don’t even know his name… Fuck, snap out of it WInchester, you can do this, casual sex is nothing compared to having your kneecaps broken right? And objectively, this guy is pretty hot: dark sex hair, probably works out, and fuck if that lip ring and those blue eyes didn’t intimidate and interest me… Yeah I could totally do this! _

 

“Well, as long as you buy me dinner first!” Dean chuckled weakly, trying to make light of the situation. The man tilted his head and squinted at Dean, which,  _ no, that was not extremely hot, not at all, come on Dean, focus! _

“ Tomorrow night then, 7. You can pick me up in your car, seeing as yours doesn’t have profanities etched into its paint. We will go to the Roadhouse, I hear they have excellent burgers; does that sound satisfactory?” 

 

_ Geez, this guy doesn’t waste any time, don’t know if I should be flattered or creeped out… _

 

“Sure, dude, that works for me. So like, do you live close to here, or..?”

The man pointed at the house across from Dean’s.

“That is my residence, right across from yours.” He smiled, “It's late, I am going to go back home. I will see you tomorrow night Dean.” The man turned to walk away.

 

“Wait,” Dean called in a fit of confidence, “I, um well I don’t know your name, I think it would make it easier to call you that instead of what I was calling you in my head?”

The man smirked, his mouth lifting at the corner, lip ring standing out in the streetlights.

 

“I’m Castiel. Novak,” he moved to turn back around but stopped, staring at Dean again, “And Dean? Wear something nice tomorrow, not that black doesn’t look good on you, but I’d love to see that cute ass in something better than those horrendous sweatpants.” Castiel winked, stalking off to his house.

 

Dean just stared after him, frozen in shock from the backhanded compliment, and the events of the  past 10 minutes.

  
_ Fuck, I’m a cheap whore _ , Dean internally groaned, walking back inside and faceplanting into his bed.


	3. Chapter 3

**Summary for the Chapter:**

> So... this is a long one, also it is frusteratingly smut-free. I kind of wanted to develop the characters a bit, and I didn't want you guys to suffer through a 3,000+ word chapter just to get to the sexy times. I am literally writing the smut as I type this, so it will be up either later tonight, or tomorrow before noon!

“ So, let me get this straight, you, Dean  _ no Charlie I don’t want to date right now _ Winchester, has a date tonight. But oh, no, it’s not just some date, it’s a date with a complete stranger, who up unitl yesterday you thought was the biggest douchebag this side of Kansas? WHY. Why did you ever think this would be a good idea?” Charlie practically screeched into the phone.

 

Dean was basically in the same position he fell asleep in last night: face down on his bed, wallowing in self-pity and uncertainty. He knew that he couldn’t tell Charlie the whole story of what happened last night; that he basically got propositioned to repay Mr. Douch- wait,  _ Castiel _ , with sex. Yeah, that would not go over well with Charlie, so Dean decided to tell a half-truth, that he was going to dinner with Castiel, who asked him out after their  _ misunderstanding _ from last night. So it was basically the whole story, only with one small detail left out, right? 

 

“Yes Charlie I have a date tonight, am I so fugly that it’s that hard to believe?” Dean pretended to scoff, “Like I told you, after Castiel hung up on you last night he told me that he only parked there because he was trying to get my attention. He, erm, thought I was cute, or whatever, and wanted to ask me out. So he did. End of story. Like I keyed the man’s car, the least I can do is go on one date with him, ya know?”  _ Or, ya know, offer him my body as an alternative payment, _ Dean brooded.

 

“Okay… I guess it is kinda sweet that he had a crush on you, and all’s fair in love and war, right? But now the real question is what are you going to wear tonight? You have to look crazy hot, obviously, seeing as this is your first date in almost a century!” Charlie giggled.

“For fuck’s sake, it was three years, Red, I would hardly call that a century.” Dean grumbled.

“ Yeah, yeah, you’re just avoiding the question Winchester. I was thinking, maybe that maroon sweater you have, the really soft one? And you  _ have to _ wear those jeans I bought you for your birthday last year, the ‘Spank Me, Daddy’ jeans!” At this, Dean let out a gutteral groan.

 

“God, Charlie! you’re at work right now, you can’t be saying shit like that! And anyways I am not wearing those jeans tonight, there is  _ negative _ space in those jeans to hold my dick, I feel like I’m in some medival chastity device when I wear them!” 

“But Dean,” Charlie whined, “Those jeans make your ass look so so so good! Like it’s like they were made for your ass to sit inside them! You have to wear them on your date, please, do it for me? Your bestest, most awesome friend ever?” Dean could practically hear Charlie’s pout through the phone.

 

But a memory from last night resurfaced at her words, didn’t Castiel say that he wanted to see Dean’s  _ cute ass _ ? If he was doing this  _ arrangement,  _ then shouldn’t he look as attractive to Castiel as possible.  _ Ugh,  _ Dean lamented,  _ I can’t believe that I’m objectifying myself for this guy. _

“Fine. You win, I’ll wear those - the jeans, that you bought me. But only because they would look good with my sweater.”

 

“Oh I’m sorry Dean, I completely blanked out,  _ which jeans exactly _ are you talking about? You’re going to have to describe them to me?” Charlie said innocently.

“Jesus, don’t make me say it Charlie, I’m beggin you here!” Dean exclaimed.

“Sorry, no dice Winchester, you are going to have to tell me what you’re talking about exactly for me to understand.” 

“Ugh, fine. The ‘Spank Me, Daddy’ jeans. Are you happy now?” Dean mumbled, completely mortified that he called this crazy woman his friend.

“OH! Yeah now I remember, thanks  _ so much _ for clearing that up for me Dean.” Charlie laughed maniacally.  _ Who’s the crazy one now, Red? _ Dean thought.

 

“Anyways… I still have a few hours to get ready, why don’t you tell me all about the hottie you met at the club the other night?” 

“Oh, dude, she was fucking smoking! Long blonde hair, tan skin. Her name’s Gilda…”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

At 6:57, Dean was parked in Castiel’s driveway, waiting for him to come outside. He didn’t have his number, so Dean hoped that he would just come out at 7. Just as he was thinking about going to ring the bell, Castiel came outside, and Dean’s eyes widened in surprise. Castiel looked  _ good _ : He was wearing black skinny jeans tucked into dark boots, with a leather jacket over a jean shirt. His eyes looked even more blue than they did last night, and his lips split into a wide smile when he spotted Dean in his driveway. Dean found himself starting to smile back, but caught himself quickly.

_ This is nothing more than a glorified business deal Dean, just because he is going to enjoy himself does not mean you have to.  _ Dean reprimanded himself. He just needed to be civil through this dinner, then let him fuck him. Dean was under no illusions; he knew that Castiel would not take sex as repayment unless  _ he _ was the one bottoming. Dean’s thoughts were interrupted by the creak of the passenger door opening.

 

“Hello, Dean, I hope you're hungry, because I certainly am.” Castiel greeted, sliding into the car and buckling his seatbelt.

“Yeah, hi Castiel. Of course, I’m never one to turn down free food,” Dean paused, realizing what he was implying, “Unless, of course, we're going dutch on this? What was I thinking of course we are, I can’t expect you to pay for my food, I can at least buy my own dinner..” Dean awkwardly chuckled, putting his foot in his mouth not even 5 minutes into the night.

“Dean, I was not expecting for you to pay for your own meal. Consider this me taking you out to get to know you, before we continue with our arrangement.” Castiel spoke plainly, not at all phased by Dean’s obvious awkwardness.

“Yeah, okay, sure. Let’s, uh, get going ya?” Dean voiced, starting the car and driving towards The Roadhouse.

 

The whole car ride, Dean could see Castiel staring at him out of the corner of his eye, which was quite unnerving to him, yet Castiel continued to stare, with that  _ sexy -  no not sexy, creepy, yeah creepy. Jeez, Winchester, get a grip _ \- squint and head tilt. Let’s just say that calling the drive ‘sexually-charged’ would definitely be an understatement.

 

Castiel held the door open for Dean once the got to the restaurant, which made Dean falter a step before entering the building, clearly not expecting that kind of treatment from Castiel.

“Dean! Haven’t seen you around her for what feels like ages, baby!” A older brunette lady beamed at him when he went up to the service desk.

“Hiya, Ellen! I know, life has just been catching up with me ya know? But you’re looking well, how’s Jo been? Keeping her nose clean I hope” Dean smiled, sending his pseudo-mother a quick wink.

 

“Oh you know my girl, always going on these damn trips all over the world! Last week she was climbing Everest with her current beau, fuckin’ Everest!” Elle laughed. That was when she noticed the man standing with Dean. He did not look like the typical Roadhouse clientel: dark hair, piercings and was that eyeliner on his eyes? Ellen hoped for Dean’s sake that the man’s bark was worse than his bite.

“Well, let me seat you and your fella over here and I’ll get Ash to bring you out some menus and drinks, ya?”

 

Dean and Castiel sat in a booth towards the back of the diner, a cosy space that further reminded Dean that this dinner was not supposed to be the romantic evening everyone was making it out to be. After Ash brought out their menus and took their orders - surprisingly, they both ordered double cheeseburgers with fries - the two men were stuck in an awkward slience. What did one talk about with a man he was going to take up the ass, not by choice, later that night?

 

“So, uh, I’m guessing we should like discuss terms or something?” Dean stated abruptly, breaking the somewhat awkward silence between them. Castiel squinted at Dean for a few seconds, before recognition crossed his face.

“Oh yes, for our agreement. Well, I was thinking it could be relatively informal, what with both of us working on different schedules, it would be inconvenient for us to couple during the day. I propose maybe, two nights a week? Of course if there were  _ needs _ either of us had outside of those days, I’m sure we can both compromise something. Anything you want to offer?” Castiel smirked, as his speech progressed, Dean’s jaw fell open more and more until he was sure it was going to hurt like a bitch to close it back up.

 

“Um, me? Yeah, yeah okay so basically the normal things: you have to wear a condom at all times, no bruises or scratches where clothes can’t cover, and when I say stop you better fucking stop.” Dean internally facepalmed himself,  _ normal things? How is discussing booty call terms any sort of normal? God damn it. _

 

Dean was saved from further conversation when Ash finally brought out their orders. Happy that he would have at least a good 20 minutes of silence due to the eating, Dean cherrily went to pop a french fry in his mouth when he heard what he could only describe as a  _ pornographic _ moan coming from across the table. Castiel had his head thrown back, chewing on a huge bite of his burger, looking like he was eating Ambrosia itself. On anyone else, Dean would have been repulsed, the loud noises and the obnoxiously exhaggerated chewing normally a turn-off.

 

But Dean could not stop  _ staring _ . 

“Liking what you see, Winchester?” Dean refocused his mind; Castiel was smirking at him, with the grease from his burger making his lips look soft, and _ pink, and so plush and biteable… _

“What, no, what do you mean? I just never saw someone get so intimate with their food before, its a little creepy dude, and I’ve seen some creepy shit.” Now it was Dean’s turn to smirk, finally one good comeback!

“Mmhm, okay. Eat, up though. If you think me eating looks ‘intimate’,” Castiel pitched his voice even deeper, sandpaper over silk, “ you should wait until I have something else in my mouth tonight.” Dean sputtered over his drink at that statement, earning a knowing look from the blue-eyed man.

“Hurry up and eat, by the way. Your food is going to get cold.” Castiel resumed eating his meal, making much less audible noises, to Dean’s relief.

 

Not much conversation continued once Dean started eating his food. Castiel called for the cheque after Dean’s last bite, paying the bill and ushering Dean out of his seat to exit the restaurant. Reaching the front of house, Dean waved goodbye to Ellen, and went to leave, but stopped when he saw Castiel stood beside Ellen.

“Thankyou very much for your hospitality Ms. Ellen, your burgers are delicious, and I will be frequenting this establishment with Dean now that I know how amazing it is.” Castiel murmered, holding Ellen’s hand between two of his. Blushing scarlet, Ellen waved off Castiel, telling him he was always welcome at the Roadhouse, and to have a good night with his “fella”.

 

“That, was… really nice of you dude,” Dean praised, walking to the car with Castiel in tow, “Ellen is pretty sweet on you now.” Castiel made an noncommential noise, sliding into the car.

Dean rolled his eyes,  _ bipolar punk-dick _ , he scoffed. 

Getting in and starting the car, Dean turned to Castiel.”So to officially start the night, my house, or yours?” Jokingly winking at Castiel, Dean secretly prayed that it would be the latter.

“Yours I think,” Castiel responded, “my brother is currrently crashing at my house for the week, and I do  _ not _ want to be disturbed tonight.”

Dean nodded, and put the car into park, driving towards their neighbourhood.

  
_ Okay, this is happening, the main event, Dean’s Big Dicking if you wanna get fancy,  _ Dean rambled,  _  I hope my room is clean and shit… Oh fuck! I swear to God if I left my bag of Cheetos on the bed I will literally die... _

**Notes for the Chapter:**

> Please don't forget to give Kudos and write me comments! It truly motivates me when ya'll interact with me! Constructive criticism is encouraged, but you can also just write me cute little messages too because yay friends!!


	4. Chapter 4

**Summary for the Chapter:**

> SMUT! Finally! This is my first attempt at writing smut, so if it's not the greatest, my bad. Hopefully you guys like it, but I am open to suggestions for later chapters! Also, holy shit balls guys, 200 hits?!?!?!?!?!?!?! You are all beautiful and I love you!

Pulling up to his house, Dean cut the engine and moved to open his car door. Too quick for him to realize, Dean felt a warm heat against his back and beck; Castiel had unclipped his seatbelt and slid across the bench seat to plaster himself to Dean. He was currently rubbing his nose along the back of Dean’s neck, occasionally pressing kisses to the sensitive skin, and running his hand up and down Dean’s side, causing him to shiver and lean his head back against Castiel’s shoulder.

“As much as I love this, Dean, I think we should move this to inside your home, unless you have a Exhibitionist kink you want to explore?” Dean could feel the man smiling into his neck. 

Unfreezing, Dean slowly pushed open the car door, dragging himself, and Castiel out of the car and towards the front door.

 

Dean went to unlock his front door, but he was having some difficulties. Castiel was still holding him from behind and kissing his neck, but now his hands had migrated to his stomach and under his sweater, long fingers running whisper-soft over his skin, causing goosebumps at an alarming rate.

“Dude, I, I need to open the door,” Castiel did not stop his ministrations, “come on man, at least let us get inside before you have your wicked way with me?” Dean sighed exasperatedly when Castiel finally stopped, taking a few steps away from Dean and raking his fingers through his already mussed up hair. Finally opening the door, Dean was rushed inside and hands were immediately pulling at his sweater.

“Stop, for fuck’s sake, let me take a moment to take of my damn shoes, Novak!” Dean hissed, swatting away greedy hands and bending down to remove his black Docs. 

 

When he felt a wandering hand creeping towards his backside, Dean growled a threatening, “If you don’t take your hands off me and take off your damn shoes I swear to all that is holy…”

“Calm down, Winchester, I was getting there, I was just appreciating the goods. Your ass looks fan-fucking-tastic in these jeans, by the way. I almost don’t want to take them off. Almost.” Castiel sneered, toeing off his worn boots and shedding his leather jacket onto the bench by the door.

Standing up right, Dean looked Castiel over; his eyes were bright with excitement, and a grin was stretched across his face.  _ Huh,  _ Dean thought, _ smiling looks good on him. _

“My bedroom is upstairs,” Dean jerked his head towards the staircase, “so follow me, or whatever.”

 

Ascending the stairs, Dean stumbled when he felt Castiel grab onto his ass once again, but he let it slide, knowing that if he kept rejecting his advances, this night would never be over. Stepping into Dean’s room, the two men turned towards each other, finally eye to eye ever since leaving the Roadhouse. Castiel’s eyes roamed Dean’s body, before his blue eyes came to rest on weary looking green ones.

“So, am I now allowed to have my ‘wicked way’ with you, Dean?” Castiel bit his lip, looking at Dean like he truly wanted to  _ ravage _ the man.

 

“Sure… I guess this is the part where I strip down and ‘assume position’ right?” Dean deadpanned, secretly nervous about what was to one of the weirdest nights of his life.

“Be my guest, babe, I’ll just stand here and watch.” Castiel leaned up against the wall, crossing his arms and showing off his impressive biceps.

 

Dean quickly and efficiently stripped off his clothing, making sure to keep accidental eye contact with Castiel to a minimum. After toeing off his socks, Dean climbed onto the bed, getting onto all fours. Squaring his shoulders, Dean prepared himself for what he was sure was going to be the least gratifying sex he ever had.  _ It’s fine Winchester, the point of this is not for  _ you _ to enjoy, its so you don’t have to shell out money you don’t have on some stupid shit you did on impulse. It won’t hurt that much,  _ Dean reassured himself,  _ I prepped myself a bit before, hopefully Castiel isn’t hung like a fucking horse or something… _

 

“Ok man, I’m ready, just like remember to wear a condom and you can do whatever you want.” Dean said, trying to sound neutral but knowing he sounded nervous as hell. When Dean didn’t hear any movement behind him, he turned his head to look back. Castiel was frozen in his spot, staring at Dean like he didn’t know what to do.

“I, uh, already prepped myself man, if that’s what you’re worrying about. You can just get on with it; though I would appreciate if you took off your clothes too, I already feel like a bit of a perv.” Dean chuckled and turned back around. He heard the rustle of clothing hitting his bedroom floor, and soon enough, Dean felt the bed dip, and the heat of Castiel’s body radiating over his back. 

 

But instead of the spread and push-in he expected, Dean felt warm hands caressing his sides, and kisses being placed down his spine. Dean shivered, it had been too long since a lover had touched him like that…but Castiel was not his lover, he was a business deal.

“Dude, what are you doing? I’m not some chick, I don’t need foreplay and shit to get wet, that’s what lube is for. Just fuck me already!” He huffed, why couldn’t Castiel just hurry this up already?

“Dean, I am just trying to make this comfortable for you, I-” Castiel was gliding his hands down Dean’s stomach, when he reached Dean’s less-than-interested cock.

“You, you’re not aroused?”Castiel asked incredulously.

 

“Um, no, but that’s okay man, just have at it, I’m good. I don’t need this to be some romantic production.” Dean squirmed uncomfortably, causing Castiel’s hand to tighten on his length. In the blink of an eye, Dean was flipped onto his back, Castiel staring back at him with his blue eyes burning with emotion.

“No. Dean I don’t want to just  _ molest _ you. I want you to have pleasure in this as well. When I thought up this arrangement I wanted it to be a give and take: you would give me pleasure of course, but you should also be taking pleasure from my ministrations.” Castiel explained, “You _ will _ receive pleasure from this Dean, if you just want to lay there like a glorified sex doll, then I would rather you just pay me for my car now and call it a day.”

 

“No! No, Castiel, I, I can do this.  _ We  _  can do this, I promise.” Dean sputtered. He lay back and spread his legs enough so that Castiel could fit in between them, and took a deep breath. “Just, come here man. Make me, um, feel good.” Dean blushed and pulled Castiel down towards him. 

 

Castiel moved towards Dean’s lips, But he lightly pushed him towards his neck instead, muttering a soft ‘ _ no kissing, at least not this time’ _ . Castiel obliged, placing kisses down his throat, occasionally lightly sucking the skin between his lips. Dean tilted his head back to give Castiel more room, lifting his hands up to let them roam around Castiel’s back muscles, testing the give by digging his fingers into the firm muscle and skin. Castiel groaned slightly, moving lower down to Dean’s chest, lifitng one hand to tweak his nipple.

Dean hissed and arched his chest away from the hand. Castiel looked up at him quizzically, asking if he was okay.

 

“Sen- senitive. Doesn’t hurt, just be more gentle, maybe use your, um, mouth?” Dean ran his hand through the hair at the back of Castiel’s head, gently guiding his lips to his nipple. He sucked Dean’s nipple into his mouth, causing Dean to whine and push Castiel’s head more firmly into his chest. Castiel took that as a signal to go crazy; licking over his nipple rapidly, pulling off with a wet pop, only to latch onto the other neglected one, tweaking Dean’s spit soaked nipple between his forefinger and thumb. 

“Uhngg, Castiel! Yes, feels so good.” Dean mumbled, feeling his cock start to thicken.

“Yeah? You like me sucking on your pretty tits ,Dean? I knew you would, so sensitive babe, you taste good too.” Castiel rasped, reaching down to feel Dean’s now hard cock, grunting happily when he wrapped his hand around the length.

 

“Nice, and hard for me Dean? Gotta taste you here too, see if you taste just as good, maybe better?” Castiel moved down the bed, and spread Dean’s legs wider, stroking Dean’s cock and staring up at him the whole time.

“Wha, oh god Castiel, are you going to? OHMIGOD Fuck!” Dean yelled, as Castiel started kissing the head of his aching cock, and quickly swallowed it down to the root. Castiel moaned around Dean, cupping his balls and lightly squeezing, causing Dean to spaz his legs out, being overloaded by the sensations. “ Castiel, feels so good, but, lower, your- your hand, go lower  _ please.”  _ Dean begged , spreading his legs even wider, exposing his hole to the man above him. Castiel pulled off Dean’s cock, grinning up at him, his pupils almost completely blown, only a thin ring of that intense blue remaining. He pushed Dean’s thight up and back, hooking his calves over his shoulders, bringing him to eye level with Dean’s twitching hole.

 

“Mmhmm, look at that pretty pussy, you want me to eat that pussy out Dean? You would like that huh?” Castiel’s voice was pure gravel at this point, causing Dean to moan and try to spread his legs even wider.

“Please, please just do it. Please  _ I need it _ .” Dean whimpered, jolting when he felt a wet tongue ghost over his hole. This seemed to flip a switch in the blue-eyed man, who proceeded to press his face into Dean’s ass, eating his hole like it was his last meal. Dean couldn’t keep still after that, thrashing on the bed and pulling on the sheets, awash in the sensations of  _ hotwetgood _ he was feeling. Soon he felt a finger rubbing at his rim, and then entering him. 

 

At the realization that Dean was already lubed up inside, Castiel growled and bit at the inside of Dean’s asscheek. “Oh God, Dean. Your pussy is still wet inside, so ready for me, probably don’t even need my fingers do you?” Castiel questioned, grinning when Dean violently shook his head.

“No, Castiel, just need you in me, please. I need your cock in me, wanna come around your cock!” Dean grittted out, his eyes hooded with the intense pleasure he was feeling. Before he was finsihed his last sentence, Dean was once again flipped over onto his stomach, his legs spread and a pillow slipped under his hips.

“Are you ready for me, Winchester? I’m going to wreck you for anyone else Dean, make it so no one else can make you come like I can.” Castiel promised, rubbing his latex-covered length over the expanse of Dean’s asscrack, catching the head on his rim every few times, punching whimpers out of Dean each time. 

 

“Yes, yes I’m ready, I’ve  _ been  _ ready, stop teasing me please!” Dean yelled, finally feeling the bloated head of Castiel’s cock breach his hole. It burned a bit, because hell if Castiel wasn’t actually hung like a  _ fucking horse _ ! But Dean was loving it, pushing his ass back onto his cock, determined to have Castiel bottom out in him.

 

“Oh fuck, Dean, baby, you take it so good. Damn your ass is so tight, squeezing me like it was made for me. Shit, yeah!” Castiel cried, pushing into Dean at an excruciatingly slow pace, when all he wanted to do was pound Dean into the mattress. Once he finally bottomed out, Castiel stilled his hips, stroking his hands down Dean’s sides and stomach, pressing kisses into the tightness of his shoulder blades and spine, trying to placate him while his body adjusted to Castiel’s sizeable length.

“Castiel, I, I’m good, you can move now...” Dean whispered, feeling like his entire body was a livewire. Castiel slowly pulled out almost all the way, and pushed back inside in one long thrust.

 

“Fuck! Yeah, give it to me, please!” Dean screeched like a hellcat, clawing at the sheets and rocking back and forth to try and get more of that sensation. After, what he did was received with near aplaud, Castiel let go: thrusting in and out of Dean long and hard, increasing his pace the louder Dean got. At one point, Castiel shifted on the bed, trying to achieve a different angle and Dean screamed in pleasure. 

“Oh, yeah. Did I hit that spot baby? You have no idea how good you feel, how sexy you look and sound, making those noises for me, Dean. Do you think you can come from just this, huh?” Castiel leant over Dean, almost chest to back, thrusting into Dean’s prostate almost ever thrust.

 

He reached under Dean’s chest and started to pinch and roll his nipples between his fingers, knowing that Dean must be close, if the noises he was making was any indication. 

“Shit, yeah Castiel, I can do it, just keep fucking me harder please, I’m almost there, so close! You’re so good, so good inside me!” Dean mumbled, half not aware of what he was really saying, high off the pleasure Castiel was giving him. Castiel nosed at the slightly sweaty nape of Dean’s neck, placing kisses on the hot flesh.

 

“You feel so good as well, Dean. You know, I wish I could come bare in you, shooting my load inside your perfect pussy. Maybe, next time, next time I can come in you, and you know what I’ll do after, babe?” Castiel purred, smirking at Dean’s questioning whimper. “ I would pull out, spread your sexy legs and  _ eat all my come right out of you. Every. Single. Drop. _ ” Castiel breathed, feeling Dean lock up on the beginnings of his orgasm.

 

“Oh Shit, Jesus, I’m, oh God! Coming, I’m coming, Cas!” Dean yelled hoarsely, spurting onto the bedsheets below Castiel. Castiel was starting to lose control as well, Dean’s ass milking the orgasm out of him.

“Yes, yes Dean, Fuck! Baby, you’re so perfect!” Castiel roared, spilling into the condom inside Dean. Castiel slowly pulled out of Dean, rolling onto his back beside him. Shortly after, Dean sleepily turned towards Castiel, rolling onto his side and lying his head on his chest.

 

“That was...nice.” Dean grinned, running his fingers over Castiel’s abs. 

“Mmhm,” Castiel agreed, “You called me ‘Cas’, when you were coming.” He abruptly stated

“Yeah, well,” Dean huffed, cheeks pinking adorably, “I was coming my brains out, and ‘Castiel’ is a mouthful even when I’m fully aware of my surroundings. So yeah, you’re Cas now, no takebacks.” Dean started drifting off, cuddling more into Castiel’s side, pulling his arm around his back.

“Okay, Dean, whatever you say…” Castiel joked, pulling the blanket up over the both of them.

  
_ I have no idea how I’m going to keep this professional,  _  Castiel thought, falling asleep the quickest he had in months. 


	5. Chapter 5

**Summary for the Chapter:**

> HOLAYYY SHIT GUYSSS!!!!!!!!!!!! 400 Hits?? Seriously  
> This started out as a quick piece i wrote while I was waiting to go into my class at uni, now its some crazy multi-chapter thing that I am super proud of!  
> I love all you beautiful flowers and your continued support, kudos and love!

**Notes for the Chapter:**

> Special shoutout to SupernaturalMystery306 (sorry babe i cannot link thinks for shit), who has really motivated me to create this chapter faster than I though I would.  
> I hope you can find the hidden line in the story that you 100% have inspired me to write!  
> Love and kisses babe! xoxo

Dean awoke to a dick poking between his asscheeks. There was no mistaking what it was, he was all too used to it when he was with Michael - having forgotten to put on clothes after an intense love-making session, they would wake up naked and horny… But the man in bed wasn’t Michael,  _ thank God, dude was a dick _ , it was Castiel... Cas. Dean internally sighed, last night was amazing: Castiel knew exactly how to touch him and brought him off in an orgasm so explosive that he almost didn’t think it was real. And the  _ dirty talk _ , Jesus if that didn’t open up a whole new can of kinks Dean had never thought about exploring. Feminization never turned Dean’s crank exactly, but Castiel telling him how good his ‘pussy’ felt last night had him blushing and squirming in the dark-haired man’s arms. Which were wrapped around him like a straightjacket: tight, unyielding, a little bit sweaty and leaving Dean feeling like he was the definition of little spoon. 

 

_ Fuck, I have an itch on my back but I can't reach… _ Dean internally whined, squirming back against Castiel’s chest, trying to get some friction against his back… and then he remembered why he woke up. 

 

Castiel’s morning wood was hot against his rear, slightly turning Dean on, and making him feel slightly mischievous; he was going to get Castiel back for last night in the car, and on the porch… and in the foyer… So Dean started grinding his ass back against Castiel’s length, hissing when his sore hole caught on the head every couple moves. Dean could feel Cas’ dick getting harder, and bigger,  _ fuck how did I fit this in my ass last night _ , Dean giggled to himself,  _ my ass is fucking amazing!  _ Slowly, as he was just becoming aware of his surroundings, Dean felt the arms encircling him start to tighten. He began to grind back against Castiel harder, starting to get aroused, and making small not-whimpers at the feeling of Castiel’s cock against his sensitive hole.

 

“ _ Dean, what are you doing? _ ” Castiel growled, his gravel rough voice sounding even rougher in the early morning hours. His arms momentarily squeezed Dean even tighter, and then migrated down to hold his hips still, prompting a petulant whine from the blonde man. 

“Cas, I, I want, I  _ need _ , please more” Dean said, arching against Castiel, pushing his hips back even as the man kept a strong hold on him, preventing him from moving. Castiel chuckled into his hair, stroking Dean’s hip bones, causing him to shiver and allowing him to continue slowly grinding back against his length. 

 

“Dean,” Castiel groaned, moving one hand back and palming Dean’s ass, “we cannot copulate this morning, you must be feeling very sore inside and-” Castiel was cut off by Dean letting out a slight hiss, he had reached Dean’s puffy hole and felt around it, knowing then that his dick was not going  _ anywhere _ in Dean’s hole that day.

“I’m, uh, okay Cas, please I gotta come, I can take you I know it.” Dean begged, having half a mind to just start jerking himself off if Castiel was not going to be useful. What happened to his whole ‘give and take’ speech from last night? Dean was  _ giving _ out his ass, Castiel just had to  _ take  _ it, it wasn’t that hard!  _ Well, hopefully it is pretty hard, kinda awkward if it's not _ , Dean smirked to himself, continuing to grind back on Castiel’s hand.

 

Castiel sighed, one night with Dean, one  _ amazing, fulfilling night _ and he was already caring about the green-eyed man way too much. He already wanted to go again, but Castiel would be damned if he hurt Dean; he wanted Dean to crave him, to want to see him, even outside their two times a week timeslots…

“Okay baby, c'mere, sit on my face, I wanna taste you.” Castiel purred, pulling on Dean’s hips to help him situate himself above Castiel on the bed. Dean looked back at Cas, biting his lip and eyes bright with arousal.

“I’ve never, sat, like,  _ sat _ on a guy’s face before. Won’t I squish the crap out of you?” Dean questioned wearily, clearly out of his element.

 

“No Dean, just get on your knees, a bit higher up, by my ears. Yeah right there, and just lower your beautiful ass down to my face, I’ll take care of you, honey.” Castiel promised, wrapping his arms under Dean’s thighs and stroking the dimples right above his ass. Dean nodded and lowered himself towards  face, holding his breath until he could feel the warmth of Castiel’s lips on the inside of his cheeks.

“Mmhmm, look at that pretty pussy, just waiting for me to get in there, ya? Gonna make you feel so good Dean.” Castiel pulled on Dean’s hips and kissed his hole, causing Dean to whimper above him. He licked around Dean’s rim, soothing the tender skin with his tongue, feeling the slight twitch his hole made every time he passed over the center. 

 

Castiel pushed his thumbs into Dean’s asscrack, pulling apart Dean’s cheeks, allowing him to go to town on the amazing man above him.

“Oh! Fuck, Cas, baby, that feels so good I, oh my God how can this feel so  _ awesome? _ ” Dean groaned, finally starting to grind down on Castiel’s face, causing Cas to grab onto his ass firmer and growl in response. Dean started to pinch at his nipples, still sensitive from the night before - he was close, and couldn’t believe just being eaten out was going to bring him over the edge this easily.  Glancing down Castiel’s body, Dean could see his hard length leaking on his stomach, making Dean’s mouth water. Reaching forwards, Dean grabbed the man’s cock in his hand, loving how  _ fucking heavy _ it felt in his hands, and began to stroke it, making sure to press against the sensitive frenulum underneath the bloated head. Moaning at the surprising stimulation, Castiel removed one hand from Dean’s ass and smoothed it up his spine from the base to between his shoulder blades,

 

“Mmhmm, Dean. Suck me, honey. Lean forward and suck that big cock, yeah, just like that…” Castiel spoke against the sensitive skin on the inside of Dean’s ass. Watching Dean bend forward and take his cock into his mouth was like heaven to Castiel; straining his neck just so allowed him to watch Dean’s pillowy lips wrap around his cock.  _ Fuck I wish I had a camera right now _ , Castiel thought, committing this view to his eternal spank bank.

 

Dean moaned around Castiel’s cock as he continued his ministrations on Dean’s hole. Even with his almost non-existent gag reflex, Dean was having a hard time taking the blue-eyed man all the way to the base. What he couldn’t fit, he fisted with his hand, the other hand snaking lower to cup Castiel’s heavy balls in his hand, the middle finger softly rubbing over his perineum. Castiel thrusted up into Dean’s mouth at that, causing him to gag and moan at the same time, feeling Castiel slyly sliding a finger into his ass as he continued to eat him out. 

“Damn, Cas, keep going, fuck my, my  _ pussy _ !” Dean moaned, popping off Castiel’s length just to swallow him back down with renewed vigor. Dean knew he was going to come soon, and he wanted Castiel to come with him… 

 

So he decided to become a damn Hoover vacuum, sucking on Castiel with all he was worth, and rolling his balls like a pro. Castiel continued to thrust into his mouth, but his rhythm was stuttering, letting Dean know he was close. And Dean knew just how to bring him over the edge.

“Baby,” Dean purred, “ I’m so close, want you to come with me! Come on, Cas, come in my mouth, _I wanna_ _taste you so badly_ …” Castiel growled and fucked his finger in and out of Dean even faster, his tongue bringing him very close to falling off the cliff. Dean pushed his finger more firmly into Castiel’s perineum, and felt his balls start to twitch, pushing Castiel over the edge. 

 

As the first hot spurt of come hit Dean’s tongue, Castiel massaged his finger on Dean’s prostate; Dean bucked wildly and came, splashing his come all over his and Castiel’s chests.

 

A few moments passed until Dean rolled over onto the mattress, turning his head to check the time on his alarm clock,  _ 8:30.  _ Dean, wasn’t exactly late to work, he started at 9:30, but now he had to take a shower to wash off the  _ everything _ from last night and now the current morning. Glancing at Castiel, Dean was met with hooded, fucked-out blue eyes, which were attached to a smirking Castiel, who was lounged back with his arms behind his head - translating into a very confortable looking human pillow.  _ I can relax for a bit before taking a shower _ , Dean rationalized,  _ he just looks so damn inviting, and I gotta thank him for that orgasm, damn. _ Dean crawled up the bed and lay beside Castiel, running his fingers through his own cooling come on the man’s stomach, massaging it into his skin with a smile on his face.

 

“Was that good enough for you, Winchester? You seemed to enjoy it if the way gobbled down my dick was any indication.” Castiel smirked, smoothing his fingers over Dean’s shoulder.

“Well, the only thing I can say, Cas, is that your name isn’t the only thing in this room that’s a mouthful.” Dean grinned mischievously, smiling wider when he received and groan and a deadpanned  _ ‘boooo” _ from the man beside him.

**Author's Note:**

> Smut will happen, my little chickens, I promise you that! Comments=coffee :)


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